ZA200604682B - Compounds for treatment of cell proliferative diseases - Google Patents
Compounds for treatment of cell proliferative diseases Download PDFInfo
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- ZA200604682B ZA200604682B ZA2006/04682A ZA200604682A ZA200604682B ZA 200604682 B ZA200604682 B ZA 200604682B ZA 2006/04682 A ZA2006/04682 A ZA 2006/04682A ZA 200604682 A ZA200604682 A ZA 200604682A ZA 200604682 B ZA200604682 B ZA 200604682B
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52887703P | 2003-12-11 | 2003-12-11 | |
| PCT/US2004/041712 WO2005058829A1 (en) | 2003-12-11 | 2004-12-13 | Compounds for treatment of cell proliferative diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200604682B true ZA200604682B (en) | 2008-04-30 |
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|---|---|---|---|
| ZA2006/04682A ZA200604682B (en) | 2003-12-11 | 2006-06-07 | Compounds for treatment of cell proliferative diseases |
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| EP (2) | EP1701941B1 (ja) |
| JP (1) | JP4751336B2 (ja) |
| KR (2) | KR101170655B1 (ja) |
| CN (2) | CN102603565A (ja) |
| AU (1) | AU2004298511B2 (ja) |
| BR (1) | BRPI0416981A (ja) |
| CA (1) | CA2548152C (ja) |
| DK (1) | DK1701941T3 (ja) |
| ES (1) | ES2385831T3 (ja) |
| HK (1) | HK1094891A1 (ja) |
| IL (1) | IL176028A (ja) |
| MX (1) | MXPA06006460A (ja) |
| PL (1) | PL1701941T3 (ja) |
| PT (1) | PT1701941E (ja) |
| SI (1) | SI1701941T1 (ja) |
| WO (1) | WO2005058829A1 (ja) |
| ZA (1) | ZA200604682B (ja) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102603565A (zh) | 2003-12-11 | 2012-07-25 | 得克萨斯州大学系统董事会 | 治疗细胞增殖疾病的化合物 |
| ZA200803226B (en) | 2005-10-13 | 2009-11-25 | Orchid Res Lab Ltd | Heterocyclic Compounds as Pstat3/IL-6 Inhibitors |
| PL2514742T3 (pl) | 2006-03-31 | 2015-07-31 | Univ Texas | Leki przeciwnowotworowe będące pochodnymi kwasu kawowego dostępnymi biologicznie po podaniu doustnym |
| WO2008005954A2 (en) * | 2006-06-30 | 2008-01-10 | The Board Of Regents Of The University Of Texas System | Tryphostin-analogs for the treatment of cell proliferative diseases |
| EP2446903B1 (en) | 2006-11-20 | 2019-10-09 | President and Fellows of Harvard College | Compositions for treating itch |
| US20080167277A1 (en) * | 2006-12-29 | 2008-07-10 | Charles Conrad | Methods of treating skin disorders with caffeic acid analogs |
| US20100144802A1 (en) * | 2007-03-28 | 2010-06-10 | Heimberger Amy B | Small Molecule Inhibitors for Immune Modulation |
| US9745278B2 (en) | 2007-09-10 | 2017-08-29 | Boston Biomedical, Inc. | Group of STAT3 pathway inhibitors and cancer stem cell pathway inhibitors |
| US8143412B2 (en) | 2008-07-08 | 2012-03-27 | Board Of Regents, The University Of Texas System | Inhibitors of proliferation and activation of signal transducer and activator of transcription (STATs) |
| US8450337B2 (en) * | 2008-09-30 | 2013-05-28 | Moleculin, Llc | Methods of treating skin disorders with caffeic acid analogs |
| US8858916B2 (en) | 2008-09-30 | 2014-10-14 | Mallinckrodt Llc | Metal chelate linked to a hexose carrier for use as a metallopharmaceutical diagnostic or therapeutic agent |
| US20120021941A1 (en) * | 2009-01-12 | 2012-01-26 | The Board Of Regents Of The University Of Texas System | Blood test for the detection of cancer |
| CA2767646C (en) | 2009-07-10 | 2019-01-29 | President And Fellows Of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| MX2012004363A (es) | 2009-10-16 | 2012-05-22 | Bayer Cropscience Ag | Aminopropenoatos como fungicidas. |
| EP2506852A4 (en) | 2009-12-04 | 2013-06-19 | Univ Texas | INTERFERONTHERAPIES IN COMBINATION WITH BLOCKING OF STAT3 ACTIVATION |
| EP2544686A4 (en) | 2010-02-05 | 2013-06-26 | Whitehead Biomedical Inst | COMBINED METHODS FOR THE TREATMENT OF DISEASES |
| CN103025159A (zh) | 2010-03-19 | 2013-04-03 | 波士顿生物医学公司 | 靶向癌症干细胞的新方法 |
| AU2011305315A1 (en) * | 2010-09-24 | 2013-03-28 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| EP2510787A1 (en) | 2011-04-15 | 2012-10-17 | Bayer Cropscience AG | Propenoates as fungicides |
| EP2716626A4 (en) | 2011-05-27 | 2014-05-07 | Univ Tokushima | benzylamine |
| WO2013009872A1 (en) | 2011-07-11 | 2013-01-17 | The Regents Of The University Of Michigan | Multimodality left atrial appendage occlusion device |
| CN105120854B (zh) * | 2012-05-25 | 2019-04-09 | 多伦多大学管理委员会 | 新水杨酸衍生物、其药学上可接受的盐、其组合物以及其使用方法 |
| US10130632B2 (en) | 2012-11-27 | 2018-11-20 | Beth Israel Deaconess Medical Center, Inc. | Methods for treating renal disease |
| WO2014169078A2 (en) | 2013-04-09 | 2014-10-16 | Boston Biomedical, Inc. | Methods for treating cancer |
| US20160367627A1 (en) * | 2013-07-02 | 2016-12-22 | Nikolai Khodarev | Anti-tumor therapy |
| US9868736B2 (en) | 2013-10-10 | 2018-01-16 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| WO2016069906A1 (en) | 2014-10-29 | 2016-05-06 | Massachusetts Eye And Ear Infirmary | Efficient delivery of therapeutic molecules to cells of the inner ear |
| CA2994545A1 (en) | 2015-08-03 | 2017-02-09 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use |
| WO2018102427A1 (en) | 2016-11-29 | 2018-06-07 | Boston Biomedical, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| JP2020520923A (ja) | 2017-05-17 | 2020-07-16 | ボストン バイオメディカル， インコーポレイテッド | がんを処置するための方法 |
| AU2018366270B2 (en) * | 2017-11-10 | 2023-04-20 | Board Of Regents, The University Of Texas System | Caffeic acid derivatives for treating hyperproliferative diseases |
| WO2019148067A1 (en) | 2018-01-26 | 2019-08-01 | Massachusetts Eye And Ear Infirmary | Treatment of hearing loss |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| BR112021017809A2 (pt) | 2019-03-11 | 2021-11-23 | Nocion Therapeutics Inc | Bloqueadores de canais iônicos substituídos por éster e métodos para uso |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2020185830A1 (en) | 2019-03-11 | 2020-09-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CN113811305A (zh) | 2019-03-11 | 2021-12-17 | 诺西恩医疗公司 | 带电的离子通道阻滞剂及其使用方法 |
| US20220175744A1 (en) * | 2019-04-02 | 2022-06-09 | Board Of Regents, The University Of Texas System | Combinations of transcription inhibitors and immune checkpoint inhibitors for treatment of disease |
| TW202106676A (zh) | 2019-04-05 | 2021-02-16 | 美商凱麥拉醫療公司 | Stat降解劑及其用途 |
| JP7513713B2 (ja) | 2019-11-06 | 2024-07-09 | ノシオン セラピューティクス，インコーポレイテッド | 荷電したイオンチャンネル遮断薬および使用方法 |
| BR112022008575A2 (pt) | 2019-11-06 | 2022-08-09 | Nocion Therapeutics Inc | Bloqueadores de canal iônico carregado e métodos para uso |
| AU2021236130A1 (en) | 2020-03-11 | 2022-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CN115381822A (zh) * | 2022-05-11 | 2022-11-25 | 暨南大学附属第一医院（广州华侨医院） | 一种基于激活免疫应答治疗肺癌的药物及制药应用 |
| KR20230175010A (ko) * | 2022-06-22 | 2023-12-29 | 한국생명공학연구원 | 신규한 신남아마이드 유도체 및 이의 용도 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2555789A1 (de) * | 1975-12-11 | 1977-07-07 | Hoechst Ag | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| FR2629455B1 (fr) * | 1988-03-29 | 1991-09-27 | Rhone Poulenc Agrochimie | Derives de 2-(3-pyridinyl)3-(phenoxy) propanenitrile |
| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| US5196446A (en) | 1990-04-16 | 1993-03-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Certain indole compounds which inhibit EGF receptor tyrosine kinase |
| JPH05507072A (ja) | 1990-04-16 | 1993-10-14 | イッスム リサーチ ディヴェロプメント カンパニー オブ ザ ヒーブルー ユニヴァーシティ オブ エルサレム | Ｅｇｆレセプタチロシンキナーゼを阻害する複素環式エテンジイル化合物 |
| JPH05301838A (ja) * | 1991-10-15 | 1993-11-16 | Mitsubishi Kasei Corp | スチレン誘導体 |
| CA2080554A1 (en) * | 1991-10-15 | 1993-04-16 | Mitsubishi Chemical Corporation | Styrene derivatives |
| CA2092017A1 (en) | 1992-03-26 | 1993-09-27 | Tameo Iwasaki | Butadiene derivatives and process for preparing the same |
| US5981569A (en) | 1992-11-13 | 1999-11-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Substituted phenylacrylonitrile compounds and compositions thereof for the treatment of disease |
| JPH06247850A (ja) | 1993-02-24 | 1994-09-06 | Suntory Ltd | １２−リポキシゲナーゼ阻害剤 |
| AU7232794A (en) | 1993-07-27 | 1995-02-28 | University Of Birmingham, The | Improvements in or relating to pavements |
| GB9322781D0 (en) * | 1993-11-04 | 1993-12-22 | Roussel Lab Ltd | Aromatic amides |
| IL107736A (en) | 1993-11-24 | 2001-01-11 | Yissum Res Dev Co | Pharmaceutical composition for the prevention of septic shock and for the treatment of chronic inflammatory diseases |
| IL112205A0 (en) | 1994-01-06 | 1995-03-15 | Res Dev Foundation | Curcumin, analogues of curcumin and novel uses thereof |
| US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| WO1995024190A2 (en) | 1994-03-07 | 1995-09-14 | Sugen, Inc. | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
| GB9406137D0 (en) * | 1994-03-28 | 1994-05-18 | Erba Carlo Spa | N-substituted beta-aryl- and betaheteroaryl-alpha-cyanoacrylamide derivatives and process for their preparation |
| AU2360595A (en) | 1994-04-22 | 1995-11-16 | Hospital For Sick Children Research and Developement Limited Partnership, The | Use of benzylidene-malononitrile derivates for the treatment of leukemia |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| IL119069A0 (en) * | 1996-08-14 | 1996-11-14 | Mor Research Applic Ltd | Pharmaceutical composition comprising tyrphostins |
| US5854285A (en) | 1997-04-03 | 1998-12-29 | Natpro, Inc. | Protein kinase inhibitor |
| US6420338B1 (en) | 1997-06-13 | 2002-07-16 | New York University Medical Center | Inhibition of the Src kinase family pathway as a method of treating HBV infection and hepatocellular carcinoma |
| US6313153B1 (en) | 1997-07-25 | 2001-11-06 | Tsumura & Co. | Compositions and methods for treating nephritis and inhibiting TGF -β related conditions using pyridylacrylamide derivatives |
| US6225346B1 (en) | 1997-10-24 | 2001-05-01 | Sugen, Inc. | Tyrphostin like compounds |
| WO2000052062A1 (en) | 1999-03-04 | 2000-09-08 | Riken | Catalyst composition |
| US20020045191A1 (en) | 2000-09-15 | 2002-04-18 | Schneider Robert J. | Inhibition of the SRC kinase family pathway as a method of treating HBV infection and hepatocellular carcinoma |
| JP2003119169A (ja) | 2001-07-30 | 2003-04-23 | Shigetoshi Kadota | 細胞毒性活性を有する化合物およびそれを有効成分とする医薬組成物 |
| US6433018B1 (en) | 2001-08-31 | 2002-08-13 | The Research Foundation Of State University Of New York | Method for reducing hypertrophy and ischemia |
| WO2003045367A1 (fr) | 2001-11-30 | 2003-06-05 | Santen Pharmaceutical Co., Ltd. | Inhibiteur d'angiogenese |
| WO2003068157A2 (en) | 2002-02-11 | 2003-08-21 | The Brigham And Women's Hospital, Inc. | Kinase inhibitors and methods of use thereof |
| US7045551B2 (en) | 2002-11-22 | 2006-05-16 | Bristol-Myers Squibb Company | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
| KR20050055479A (ko) | 2003-12-08 | 2005-06-13 | 김철호 | 카페인산 또는 카페인산 페네틸에스테르를 유효성분으로하는 ｍｍｐ-9 억제제 |
| CN102603565A (zh) | 2003-12-11 | 2012-07-25 | 得克萨斯州大学系统董事会 | 治疗细胞增殖疾病的化合物 |
| PL2514742T3 (pl) * | 2006-03-31 | 2015-07-31 | Univ Texas | Leki przeciwnowotworowe będące pochodnymi kwasu kawowego dostępnymi biologicznie po podaniu doustnym |
| WO2008005954A2 (en) | 2006-06-30 | 2008-01-10 | The Board Of Regents Of The University Of Texas System | Tryphostin-analogs for the treatment of cell proliferative diseases |
| EP2104424A4 (en) * | 2006-10-30 | 2011-06-15 | Wockhardt Research Center | PHARMACEUTICAL COMPOSITIONS COMPRISING ENTACAPONE, LEVODOPA, AND CARBIDOPA |
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2004
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- 2004-12-13 PL PL04813958T patent/PL1701941T3/pl unknown
- 2004-12-13 KR KR1020067013861A patent/KR101170655B1/ko active IP Right Grant
- 2004-12-13 BR BRPI0416981-6A patent/BRPI0416981A/pt not_active IP Right Cessation
- 2004-12-13 EP EP04813958A patent/EP1701941B1/en active Active
- 2004-12-13 CN CN2004800370450A patent/CN1894215B/zh active Active
- 2004-12-13 ES ES04813958T patent/ES2385831T3/es active Active
- 2004-12-13 JP JP2006544085A patent/JP4751336B2/ja active Active
- 2004-12-13 SI SI200431908T patent/SI1701941T1/sl unknown
- 2004-12-13 DK DK04813958.8T patent/DK1701941T3/da active
- 2004-12-13 AU AU2004298511A patent/AU2004298511B2/en not_active Ceased
- 2004-12-13 EP EP12167605.0A patent/EP2487156B1/en active Active
- 2004-12-13 MX MXPA06006460A patent/MXPA06006460A/es active IP Right Grant
- 2004-12-13 US US11/010,834 patent/US7745468B2/en active Active
- 2004-12-13 WO PCT/US2004/041712 patent/WO2005058829A1/en active Application Filing
- 2004-12-13 PT PT04813958T patent/PT1701941E/pt unknown
- 2004-12-13 CA CA2548152A patent/CA2548152C/en active Active
- 2004-12-13 KR KR1020117027869A patent/KR101218633B1/ko not_active IP Right Cessation
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2006
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2007
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2010
- 2010-06-28 US US12/824,901 patent/US8119827B2/en not_active Expired - Fee Related
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2012
- 2012-01-13 US US13/350,637 patent/US8648102B2/en active Active
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2014
- 2014-01-03 US US14/147,089 patent/US9096499B2/en active Active
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